Interactions Between Quercetin and Warfarin for Albumin Binding: A New Eye on Food/Drug Interference

被引:36
作者
Di Bari, Lorenzo [1 ]
Ripoli, Silvia [1 ]
Pradhan, Sanghamitra [1 ]
Salvadori, Piero [1 ]
机构
[1] Univ Pisa, Dipartimento Chim & Chim Ind, Pisa, Italy
关键词
human serum albumin; circular dichroism; flavonoids; drug-albumin binding; STD-NMR; HUMAN SERUM-ALBUMIN; CIRCULAR-DICHROISM; DRUG-BINDING; SPECTROSCOPY; NMR;
D O I
10.1002/chir.20794
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The interaction between quercetin, a popular antioxidant flavonoid, and human serum albumin (HSA) is investigated and characterized by means of induced circular dichroism and saturation transfer difference NMR. These techiques demonstrate the reversible binding of quercetin to the carrier protein, which is responsible for its dissolution in aqueous medium. Competition experiments with two classical probes for HSA binding sites, namely Ibuprofen and Warfarin (a common anticoagulant coumarin), demonstrate that quercetin has a primary binding site located in the subdomain IIA, where coumarins are hosted. The affinity for this site is large and we found that quercetin may effectively displace warfarin from HSA. This may have relevant consequences in rationalizing the interferences of common dietary compounds and food supplements to anticoagulant treatments. Chirality 22:593-596, 2010. (C) 2009 Wiley-Liss, Inc.
引用
收藏
页码:593 / 596
页数:4
相关论文
共 18 条
[1]  
[Anonymous], 1975, PHYTOCHEMISTRY
[2]  
Anslyn E., 2004, Modern Physical Organic Chemistry
[3]   Drug binding to human serum albumin: Abridged review of results obtained with high-performance liquid chromatography and circular dichroism [J].
Ascoli, Giorgio A. ;
Domenici, Enrico ;
Bertucci, Carlo .
CHIRALITY, 2006, 18 (09) :667-679
[4]   Interaction of 7-hydroxyflavone with human serum albumin: A spectroscopic study [J].
Banerjee, Anwesha ;
Basu, Kaushik ;
Sengupta, Pradeep K. .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2008, 90 (01) :33-40
[5]   Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].
Berova, Nina ;
Di Bari, Lorenzo ;
Pescitelli, Gennaro .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931
[6]   Extensive binding of the bioflavonoid quercetin to human plasma proteins [J].
Boulton, DW ;
Walle, UK ;
Walle, T .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1998, 50 (02) :243-249
[7]   Serum albumin and natural products [J].
Di Bari, L ;
Ripoli, S ;
Salvadori, P .
PROGRESS IN BIOLOGICAL CHIRALITY, 2004, :271-295
[8]   Flavonoid-serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy [J].
Dufour, C ;
Dangles, O .
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2005, 1721 (1-3) :164-173
[9]   Structural basis of the drug-binding specificity of human serum albumin [J].
Ghuman, J ;
Zunszain, PA ;
Petitpas, I ;
Bhattacharya, AA ;
Otagiri, M ;
Curry, S .
JOURNAL OF MOLECULAR BIOLOGY, 2005, 353 (01) :38-52
[10]  
HARBORD H, 1993, FLAVONOIDS ADV RES 1